Oprah Winfrey and Stedman Graham first met at a charity event in 1986

Photo: Kevin Mazur/Getty

The couple first met at a charity event in 1986, the same year The Oprah Winfrey Show premiered. After striking up a friendship, the pair eventually started dating later that year. While they were engaged at one point, Winfrey and Graham decided to forgo marriage in exchange for a different kind of life partnership.

During an appearance on The Ellen Degeneres Show in May 2019, Graham opened up about how he and Winfrey have maintained a successful relationship by having their own identities.

1986: Oprah Winfrey and Stedman Graham first meet at a charity eventRon Galella/Ron Galella Collection via Getty

Winfrey and Graham first met at a charity event in 1986, but she was initially skeptical about the businessman. In an essay she wrote for O, The Oprah Magazine in 2020, Winfrey revealed they reconnected that same year while visiting a mutual friend.

1986: Oprah Winfrey and Stedman Graham begin datingJim Smeal/Ron Galella Collection via Getty

Despite her suspicions, Winfrey struck up a friendship with Graham. “It wasn’t until months later, when I learned he’d broken up with his girlfriend and had been inquiring about my dating status, that I gave him a serious thought,” she wrote for her eponymous magazine in 2020.

While Winfrey initially was unsure about Graham, she said in O, The Oprah Magazine that the businessman was a “genuine gentleman.”

December 8, 1986: Oprah Winfrey and Stedman Graham make their red carpet debutStedman Graham and Oprah Winfrey attend “Native Son” Premiere on December 8, 1986 at the Apollo Theater in New York City.

By December 1986, Winfrey and Graham weren’t shy about taking their romance public. They attended the premiere of Native Son at the Apollo Theatre in New York City together and were photographed holding hands. Winfrey starred in the drama film as the character Mrs. Thomas.

1987: Stedman Graham makes an appearance on The Oprah Winfrey Show

A year into their relationship, Graham made his first appearance on The Oprah Winfrey Show. During a Q&A segment with viewers, Graham surprised Winfrey by calling in to ask her what she had been telling her best friend, Gayle King, about him. The TV host immediately recognized his voice, calling him “Steddy honey.”

October 1992: Oprah Winfrey and Stedman Graham get engagedSGranitz/WireImage

1993: Oprah Winfrey and Stedman Graham call off engagementManny Ceneta/Getty

September 22, 2002: Oprah Winfrey and Stedman Graham attend the Primetime Emmy AwardsOprah Winfrey and Stedman Graham.

2011: Stedman Graham says he’s “not threatened” by Oprah Winfrey’s successJim Spellman/WireImage

In a behind-the-scenes video from Winfrey’s last few episodes of The Oprah Winfrey Show, Graham made an appearance to support his longtime partner. Winfrey mentioned in the video that “people are fascinated with the relationship” because they “haven’t seen him.”

September 2016: Oprah Winfrey shuts down rumors she married Stedman GrahamOprah Winfrey Instagram

Winfrey talked to Vogue in August 2017 about why marrying Graham was never a serious consideration despite their 1992 engagement.

Winfrey and Graham are a very private couple, and The Color Purple star opened up to Gwyneth Paltrow on her Goop podcast about why they keep their relationship out of the spotlight.

August 2018: Oprah Winfrey reveals her “perfect date night” with Stedman GrahamPaul R. Giunta/Getty

During an O, The Oprah Magazine’s “Ask a Staffer” Q&A on Instagram in August 2018, Winfrey shared that Graham is always game to eat whatever she cooks for him.

October 2019: Oprah Winfrey explains why she chose not to marry or have 𝘤𝘩𝘪𝘭𝘥renKevin Mazur/WireImage

In an October 2019 interview with PEOPLE, Winfrey shared that she has no regrets about not getting married or having 𝘤𝘩𝘪𝘭𝘥ren. The A Wrinkle in Time star explained that while she had considered becoming a mother after she and Graham got engaged, she soon realized “the depth of responsibility and sacrifice that is actually required to be a mother.”

January 2020: Oprah Winfrey discusses how she and Stedman Graham make their “spiritual partnership” workMichael Kovac/Getty

In her 2020 essay for O, The Oprah Magazine, Winfrey referred to her relationship with Graham as a “spiritual partnership.” She explained that she learned the term from author Gary Zukav, and it means a “partnership between equals for the purpose of spiritual growth.”

January 29, 2021: Oprah Winfrey and Stedman Graham spend her 67th 𝐛𝐢𝐫𝐭𝐡day togetherprah Winfrey and Stedman Graham attend Tyler Perry Studios grand opening gala on October 05, 2019 in Atlanta, Georgia.

“Thank you to all my special friends, and friends I didn’t even know I had, for your 𝐛𝐢𝐫𝐭𝐡day wishes! I felt blessed by your messages. And grateful to have another turn around the sun,” she wrote in the caption. “@stedmangraham and I had a quiet day at home watching The Autobiography of Miss Jane Pittman and Sounder and ate some cake.”